Jon Gruden Set to Leave ESPN for Oakland Raiders in $100 Million Deal

The “Monday Night Football” analyst will return to the team that he coached from 1998-2001

The modern voice of ESPN’s “Monday Night Football” is heading from the broadcast booth back to the field.

Jon Gruden is expected to sign a 10-year deal worth nearly $100 million with the Oakland Raiders on Tuesday, ESPN’s Adam Schefter has reported.

Gruden previously coached the Raiders from 1998-2001, before heading to the Tampa Bay Buccaneers in 2002 — where he ironically beat Oakland in Super Bowl XXXVII.

Gruden will replace Jack Del Rio, who was fired after the regular-season finale on Sunday.

The NFL guru nicknamed “Chucky” (because he looks like the demonic character from “Child’s Play”) has been a longtime target for Raiders owner Mark Davis, dating back to when his late father, Al Davis, owned the team.

If confirmed, Gruden’s deal will be the largest contract for a head coach in the NFL, and he will be running the most expensive coaching staff in NFL history, per NFL Media’s Ian Rapoport. Gruden’s staff are expected to get four-year contracts with at least one of those years in the Bay Area and the others coming in Las Vegas when the team relocates.

Gruden’s last game coaching the Raiders was the infamous Tuck Rule game against the New England Patriots in January 2002. Tom Brady went on to lead the Patriots to victory in Super Bowl XXXVI, and four more times since the game. The Raiders have had only one two winning seasons since Gruden’s departure.

The Raiders have yet to comment on their choice of new head coach.

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